The story follows Harold Lee (John Cho) and Kumar Patel (Kal Penn) as they decide to go to the fast food chain White Castle after smoking cannabis, but end up on a series of comical misadventures when they cannot find the restaurant.

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Investment banker Harold Lee (John Cho) is persuaded by his colleagues Billy and JD to do their work while they leave for the weekend. Elsewhere, Kumar Patel (Kal Penn) attends a medical school interview at the behest of his father but intentionally botches it to avoid getting accepted. Upon arriving home, Harold meets his neighbor Maria (Paula Garcés) but is unable to admit his feelings for her. After smoking marijuana with Kumar, and seeing an advertisement for White Castle, the pair decide to get hamburgers to satisfy their hunger. Traveling to the location of the nearest White Castle, the pair find it has been replaced by "Burger Shack" but are informed that there is another White Castle in Cherry Hill.

When Kumar becomes sober, he suggests stopping at Princeton University to buy marijuana. Kumar buys marijuana from a student named Bradley (Dov Tiefenbach) while Harold deals with Korean students who admire his job. After smoking more marijuana, Harold and Kumar are discovered by a campus security guard and are forced to flee, losing their bag of marijuana. While the guards chase the pair, they discover Bradley's bag of marijuana and have him arrested. Harold and Kumar resume their drive, and Kumar pulls over to urinate. He leaves the car door open, allowing a raccoon to sneak in. It bites Harold, who convinces Kumar to take him to a hospital where Kumar's father and older brother work. Kumar steals ID badges from his father and brother to obtain medical marijuana, but after being mistaken for his brother Kumar is forced to perform surgery on a gunshot victim. After Kumar treats the man's wounds almost effortlessly, the patient tells them how to reach White Castle and the duo continues their quest.

On the road, Kumar spots Maria. He decides to get her attention so Harold can talk to her, but Harold panics and presses the accelerator, causing the car to crash into a ditch. They are rescued by Randy, a disfigured tow-truck driver, whose nickname is "Freakshow" (Christopher Meloni). He takes them to his house to repair their car, giving them permission to kiss his wife. Harold and Kumar are propositioned by Freakshow's surprisingly alluring wife (Malin Åkerman), but after Freakshow suggests a foursome, Harold and Kumar flee in disgust. Noticing a hitchhiker along the road, Kumar decides to stop and pick him up. The hitchhiker actually turns out to be Neil Patrick Harris, who is high on ecstasy. When Harold and Kumar head into a convenience store to get directions, Harris drives away in Harold's car. The duo are then harassed by a racist police officer; Harold attempts to punch Kumar for antagonizing the officer, but accidentally strikes the officer instead.

In jail, Harold sees Bradley being released and his stash confiscated. Kumar fakes a 911 call to draw the police and breaks into the station to free Harold. As the police return, Harold and Kumar flee again, taking Bradley's stash. The pair encounters an escaped cheetah, and after smoking marijuana with it, they ride it. They realize the cheetah took them in the wrong direction and consider returning home, but when Harold and Kumar see their neighbors Goldstein (David Krumholtz) and Rosenberg (Eddie Kaye Thomas) eating at a hot dog restaurant, Harold decides he wants the feeling of satisfaction from achieving their goal. After encountering a group of sport punks who routinely harass the pair, Harold and Kumar steal their truck. A police officer spots the speeding truck and gives chase. They briefly elude the officer, but are trapped when they reach the edge of a cliff. Spotting the White Castle below, Harold and Kumar use a hang glider from the truck to reach their destination. The pair place their orders but are disheartened to find they have no money. Harris suddenly appears, and apologizes for his actions, providing them with cash for their meal and for repairs to Harold's car.

Kumar realizes he wants to be a doctor, but is afraid of conforming to the stereotype of Indians becoming doctors. As Kumar is talking Harold notices his co-workers pull up with two women and gets angry because they said they had to work with clients that night, when they were actually out partying. He confronts them for leaving their work to him, and threatens to get them fired if it happens again. After returning to their apartment they encounter Maria in the elevator. Harold professes his feelings for her and they kiss. She informs Harold that she is leaving for Amsterdam but will return in ten days. Kumar convinces Harold to go with him to Amsterdam to pursue Maria, reminding him that marijuana is legal in the Netherlands.

The film was positively received by critics, with a 74% rating at Rotten Tomatoes based on 143 reviews; the consensus states "The likable leads and subversion of racial stereotypes elevate Harold and Kumar above the typical stoner comedy."[2][3]

Acclaimed film critic Roger Ebert of the Chicago Sun-Times awarded the film 3 out of 4 stars and wrote "One secret of fiction is the creation of unique characters who are precisely defined. The secret of comedy is the same, with the difference being that the characters must be obsessed with unwholesome but understandable human desires."[4]

Both Hurwitz and Schlossberg announced plans to write a third Harold and Kumar film, with Greg Shapiro returning as producer, and Kal Penn and John Cho returning in their title roles,[5][6] While Todd Strauss-Schulson directed The film. A Very Harold & Kumar 3D Christmas, was released on November 4, 2011 in 2D and 3D.